For an hour or so, he railed about socialism and political correctness to an audience of New York establishment Republicans. As he often does, he took ugly swipes at Ivy Leaguers, left-wing snobs and lesbians with “geriatric crew cuts.”

Then, when his speech was over, Gavin McInnes stepped outside of the Metropolitan Republican Club, protected by the police. Just before a brawl broke out between his allies and a crowd of shouting protesters, he waved a plastic sword in the air, slipped into a car and sped away.

But at the center of the fray on Friday night was Mr. McInnes, the founder of the Proud Boys and a former Brooklyn hipster turned far-right provocateur.

With his egghead glasses, pocket-protector and heavy-drinking, angry-nerd aesthetic, Mr. McInnes has in recent years set himself apart from the current crop of professionally outraged right-wing pundits, not only for being able to spout aggressive rhetoric, but also for being willing to get physical at times.

His obsessions seem to be more cultural than political. Mr. McInnes, a fiscal conservative and libertarian, calls himself a champion of Western values and reserves a burning ire for the political correctness of people on the left whom he describes as busybodies who have lost their sense of humor.

“This movement is normal people trying to live their lives getting attacked by mentally ill lunatics,” he said.

But his views are darker when it comes to gender roles and immigration. Mr. McInnes admits that he may be Islamaphobic (“It’s seen as xenophobic to be worried about Islam, but they appear to disproportionately allow intolerance to blossom in their communities,” he said.) He also acknowledged being something of a sexist. (“I’m an Archie Bunker sexist,” he said. “I don’t like Gloria Steinem, but I’d take a bullet for Edith.”)

Though he has repudiated racism and anti-Semitism in some of his writings and speeches, he has also made statements that have openly denigrated nonwhite cultures. Last year, he wrote of white men: “We brought roads and infrastructure to India and they are still using them as toilets. Our criminals built nice roads in Australia but Aboriginals keep using them as a bed.”

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The Proud Boys and the 211 Boot Boys used the white power hand symbol as they posed for a photo after the brawl in Manhattan on Friday.CreditShay Horse

His critics say rhetoric like this echoes strands of white-nationalist philosophy, and that some of his followers have crossed the line at times.

“Their disavowals of bigotry are belied by their actions,” the Southern Poverty Law Center, a nonprofit organization that tracks extremist groups, wrote in an online memo labeling the Proud Boys as a hate group. “Rank-and-file Proud Boys and leaders regularly spout white nationalist memes and maintain affiliations with known extremists. They are known for anti-Muslim and misogynistic rhetoric.”

Daryle Lamont Jenkins, the founder of One People Project, an anti-racist organization, said Mr. McInnes has been allowed to tread a fine line, appearing as a political commentator on mainstream outlets like Fox News while being the founder of a group involved in violent clashes.

“They’ve utilized subterfuge and lies to keep that hate group tag from being applied to them,” Mr. Jenkins said. “Every time their members are seen doing things they’re not supposed to be doing, like showing up at Unite the Right, they claim that person left the Proud Boys.”

On television and on frequent speaking tours, Mr. McInnes, who is 48, can often sound like a younger and more foul-mouthed President Trump, bashing feminists, mocking Black Lives Matter and deriding deep-state plotters. And like the president, he tends to publicly disavow all violence while winkingly insisting that he — and the Proud Boys — will never back down during a scrape.

“We don’t start fights,” he wrote in an article last year, “but we will finish them.”

In an interview this week, Mr. McInnes said he gave his speech this weekend after he called officials at the Metropolitan Republican Club and asked for permission to appear there.

He arrived at the club’s headquarters on East 83rd Street on Friday night with a small contingent of Proud Boys who he said were there to “do security.” Deborah Coughlin, the president of the club, said that she welcomed Mr. McInnes because there had been no trouble when he spoke at the club last year. Ms. Coughlin explained that the club considered Mr. McInnes’ political views to be on the spectrum of conservative “civil discourse.” She also noted that during the event, his followers were quiet and respectful.

But according to the police, skirmishes erupted as soon as the evening’s program ended and Mr. McInnes’s supporters confronted a group of masked left-wing protesters that had left the event and walked down Lexington Avenue to catch them. The opposing forces came face-to-face on East 82nd Street, yelling at each other as they met. A protester hurled a plastic bottle at the Proud Boys, and that, the police said, was when the punches started flying.

It was not the first time that the city’s anarchists and anti-fascists have clashed with Mr. McInnes and the Proud Boys, who have often served as a private fight club ready to protect him.

In February 2017, the Proud Boys were present when anti-fascists swarmed their leader as he showed up at New York University to speak to the College Republicans there. Mr. McInnes claimed that he was doused with pepper spray during the brawl that unfolded on the Greenwich Village campus. Eleven people were eventually arrested.

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Born in England and raised in Canada, Mr. McInnes has been a controversial figure in the news media for nearly 20 years. In 1994, after emerging from the punk-rock music scene, he co-founded Vice, the Montreal-based hipster magazine that later moved to Brooklyn and delighted audiences from the start with its graphic articles on subjects such as drug-abusing models and decomposing pigeons.

While working for the magazine, he moved to Brooklyn, taking up residence in a Williamsburg apartment. He now resides in the suburbs.

After leaving Vice in 2008 because of creative differences with his partners, Mr. McInnes went on to write a series of books, like “How to Piss in Public,” and articles for right-wing websites, like Taki’s Magazine and VDARE.

Even in his earliest work, Mr. McInnes often took an adolescent pleasure in offending liberals, women, “beta male culture” and transgender people, writing in a voice inflected with a crass, contrarian bigotry that left him just enough room to declare it all a joke.

In 2016, Mr. McInnes founded the first official chapter of the Proud Boys in New York after, he said, he realized that fans of his former television program, “The Gavin McInnes Show,” liked to spend time in his studio, drinking beer with him and telling private jokes.

He has described the group, which has since spread to dozens of cities and to countries, like Australia and Japan, as an ordinary men’s club, like the Shriners or the Elks. It serves as a sort of safe space for him and what he calls his fellow “Western chauvinists.”

In its guise as a fraternal organization, the Proud Boys get together in New York and other cities once a month at beery meet-ups that can draw as many as a few hundred participants. Women are not allowed at the group’s formal gatherings (though they are permitted at the “warm up” sessions, Mr. McInnes has written). As a character-building exercise, the Proud Boys forbid both masturbation and the watching of pornography. The group’s initiation rituals include reciting the names of five breakfast cereals while being slugged by other members.

The monthly meet-ups are largely “social events where people have fun and laugh and drink and share stories about their kids and businesses and stuff like that,” said Pawl Bazile, the editor of Proud Boy magazine. “It’s a celebration of the West, of America and of freedom and liberty.”

But in the last two years, members of the group have also had a second preoccupation, taking part in a string of violent street fights with their anti-fascist rivals in cities like Berkeley, Los Angeles and Portland, Ore.

Sometimes accompanied by skinheads, neo-Nazis, modern-day Confederates and outfits like the Oath Keepers, an association of law-enforcement officers and military veterans, the Proud Boys have scuffled with the left at May Day rallies, so-called free-speech protests and at marches in support of President Trump.

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Windows were broken and anarchist symbols were drawn on the doors at the Republican Club in Manhattan ahead of Friday’s appearance by Mr. McInnes.CreditJeenah Moon for The New York Times

While the Proud Boys accept minority members, they have at times joined forces with overtly racist organizations. Jason Kessler, who once attended Proud Boy meetings in Virginia, organized the violent rallies in Charlottesville, Va., last year that attracted neo-Nazi groups.

One former Proud Boy, Rich Black, was among the planners of two violent rallies in Berkeley in 2017 that were attended by white supremacist groups.

Mr. McInnes did not go to Charlottesville and explicitly forbade the Proud Boys from attending. “To be clear, all white nationalists/anti-Semites are banned from Proud Boys even if they never bring up said topics,” he wrote in an article shortly after the violence in Virginia.

And yet, among those who attended his event on Friday night were a few alleged members of a local skinhead group, the 211 Boot Boys, and the founder of a record label called United Riot that releases albums from local skinhead punk bands. United Riot organized a fund-raiser last year for Andrew Kuklis, a Long Island member of the 211 Boot Boys who was arrested in January 2017 on firearms charges.

In a text message on Monday, Mr. McInnes denied he had connections with the 211 Boot Boys, saying, “I don’t represent them and I have no idea who they all are and what they stand for.”

He also said on Monday on his show “Get Off My Lawn,” on the CRTV streaming network, that he could not understand why the Proud Boys had been blamed for the rioting last week when Antifa had started the conflict, placing threatening phone calls to the Metropolitan Republican Club and vandalizing its property.

“Article after article has this narrative where they took a fight that happened for maybe five seconds, and they ignored the previous three days of extremist, leftist violence,” he said.

Mr. McInnes’s confusion did little to win over Republicans like William F. B. O’Reilly, who was president of the club from 1998 to 2002.

A version of this article appears in print on , on Page A21 of the New York edition with the headline: Gavin McInnes’s Path, From Hipster to Far-Right Firebrand. Order Reprints | Today’s Paper | Subscribe